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Paper | Special issue | Vol 97, No. 2, 2018, pp.823-841
Published online, 30th March, 2018
DOI: 10.3987/COM-18-S(T)58
Substituent Effects in Regio- and Stereoselective Ring-Opening Reaction of Aziridines with Et3N·3HF for β-Fluoroamine Synthesis

Shigeru Sasaki,* Satono Watanabe, Kaori Shiino, Yuko Yanaka, Shiho Kaneko, Kana Miyamoto, Ayano Yasui, Hina Sakaino, Hiroyoshi Teramoto, Takayasu Yamauchi, and Kimio Higashiyama

*Synthetic Organic Chemistry, Institute of Medicinal Chemistry, Hoshi University, 2-4-41 Ebara, Shinagawa-ku, Tokyo 142-8501, Japan


This paper discusses the reactivity of various 2-substituted aziridine derivatives. The reaction of chiral 2-aryl-substituted aziridines with triethylamine trihydrofluoride (Et3N·3HF) afforded chiral β-fluoroamines with high stereoselectivity. In contrast, the reaction of chiral 2-aliphatic-substituted aziridines with benzyl bromide, followed by treatment with Et3N·3HF, gave chiral β-fluoroamines with high stereoselectivity.